


Fun Times

by FangurlLife99



Category: Supernatural
Genre: Multi
Language: English
Status: Completed
Published: 2018-12-04
Updated: 2018-12-04
Packaged: 2019-09-07 08:09:36
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,706
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16850353
Author URL: https://archiveofourown.org/users/FangurlLife99/pseuds/FangurlLife99
Summary: Dean and Y/N are celebrating their anniversary, but Y/N wants to spice things up in the bedroom.





	Fun Times

**Author's Note:**

> Pairing: Dean x reader, Sam x reader, Sam x reader x Dean (no wincest)  
> Summary: Dean and Y/N are celebrating their anniversary, but Y/N wants to spice things up in the bedroom.  
> Warnings: Smutty smut smut smut, dirty talk, dirty thoughts, teasing, masterbation, oral sex (both male and female receiving), threesome (no wincest), unprotected sex, biting kink, sex from behind, light BDSM, swearing, sub!Dean, dom!reader, sub/dom!Sam, very descriptive, smidgen of fluff. NSFW gif under the cut.  
> Word Count: 3652

Dean and I are celebrating our 3 year anniversary today. Usually we both end up going to a nice restaurant, go to bar and have a few drinks, then end up having the best sex ever. Today though I wanted to mix things up a little bit, with permission from Dean of course.  
I wanted to throw Sam into the mix. I mean I know that he has had his eye on me long before his brother and I got together, and I can’t help but wonder what he is hiding underneath all the flannels and loose jeans, or sweatpants. Being held in here sometimes I think of things that I want that boy to do to me. Man those boys will end up ruining me with their good looks, and probably, what I can gather from having Dean, sizeable cocks.  
“Dean I have a question, and you are so totally welcome to say no if you are not comfortable.” I waltzed into the kitchen finding him at the table with a beer.  
“Sure sweetheart ask away.”  
I moved toward him to sit in his lap. I wanted to get him in the mood, so I had a slight chance of him saying yes. “I was wondering,” I started to slowly grind on him already feeling a bulge in his jeans, “if Sammy could join us tonight?” He tilted his head back in pleasure, so I abruptly stopped.  
“If you want him to join us, I’m fine with that.” He smiled up at me, and grabbed my hips.  
“Really?”  
“Anything you want sweetheart it’s yours.” I know where he was going he wanted me to keep rubbing up against him because it relaxed him.  
He still had a hold of my hips, and started to make me move over his cock again, but I jumped up before he could get any pleasure out of it. I wanted him to suffer. I wanted both of them to suffer.  
“Sorry big boy, but you’ll just have to wait.” I said walking out of the kitchen satisfied that I got him going. Now to rile up Sam.  
I walked down to Sam’s room to see if he was in there. He was in there all right, but of course he was. If he wasn’t in the library or the war room, he was in his room researching. I was hesitant to knock because if I did it would make the reality of this sink in and then I wouldn’t be able to focus on anything. I needed to focus on getting Sam riled up and in the mood just like I did for Dean.  
I knocked hesitantly, and walked in when he gave the okay.  
“Oh hey Y/N, what’s up?”  
“Oh nothing just the usual.”  
“Teasing Dean again.”  
“You know me too well.”  
“Yeah sadly I know you way too well. Somethings I don’t want to know.”  
“Like what?”  
“Like what you do to make Dean get all flustered. You know that affects me too right? I have to be able to work with him when he’s like that.”  
“I know. How else does it affect you? Maybe it makes you wish you were in his position.” I walked toward him and shut his laptop. “Me sitting in your lap, facing you,” I started to act out every word I was saying, Sam tensing up like I was reading his mind, “grinding painfully slow. Just enough to get you going, you egging me to keep going,” that’s when his tensed look disappeared and he started to relax.  
He reached up to grab my hips to get me to keep going.  
“No Sam. Not yet. I want to make both our dreams come true tonight.”  
“What about...what about Dean?”  
“Don’t worry about him. I have been waiting for this for a long time,” I whispered in his ear.  
“How long?” He could hardly speak. I had him right where I wanted him  
I stopped moving, but continued to whisper in his ear, “longer than you could possibly know. I want to know what your cock feels like when I pump up and down. I want to know what it tastes like when you cum in my mouth. I want to feel your huge cock thrust into me. I want to know how it feels to clench around it. I want you to make me cum Sam.” I had him wrapped around my finger now.  
He moved to take action the words I was saying, but I jumped up as he went to do so.  
“No Sam. We will do this my way. Meet me in my room in 10 minutes if this is what you really want.”  
I walked back to the kitchen to find Dean in the same spot where I left him.  
“Good you’re back, I was starting to think you were starting without me.” He said standing up.  
“No I had to get him in the mood. Now sit back down.” He did as he was told.  
I normally dominate as long as toys or anything aren’t involved. If they are, Dean takes the reigns. He likes that kind of thing. Me I just want to be a little controlling, things done to me the way I want them done to me.  
“Are really okay with Sam joining us?”  
“Yeah, I mean as long as I get to have my way with you too.”  
“Of course, but I want Sam to start off, and then you can join in. Only if you’re comfortable with that.”  
“Okay…”  
“Then later it can be just the two of us and you can do whatever you want to me.”  
“Okay that actually sound nice.”  
I told Dean the same thing I told Sam, but I told him he could wait till we were done before he came in.  
10 minutes rolled by and I sat waiting to see if Sam would show up if not, then I would improvise, but I didn’t want to make him do anything he wasn’t comfortable with. Finally he walked in.  
“So what do you want me to do? I know how dominating you are and I just want to do everything in my power to make you happy.”  
“You can do whatever you want to me.”  
“She gave me the same permission later.” Dean said standing in the doorway. He was shirtless, but he had on some black sweatpants and I knew what he was going to do.  
“If you don’t want him here I can send him away?”  
“No it’s fine. I just hope he doesn’t get jealous.”  
Sam grabbed me and pulled me closer to him, leaving no space between us. I wrapped my arms around his neck and pulled him down connecting our lips. His were sweet like honey and I wanted to lick up every drop. He moved his hands down to my ass and squeezed making me gasp so he could sneak his tongue into my mouth. I let him explore while I soaked in all of the sweetness.  
He started to pull at my clothes telling me he wanted them gone. He snaked his hands up my shirt to cup my breasts only to find that my bra was in the way. He pulled away for a second to unhook my bra and lift my shirt up. I mimicked him taking off his top flannel then his under shirt.  
He walked me backward toward the bad. I fell and he crawled on top of me, attaching his lips to my neck, and kissing slowly all the way down to my chest. He took one of nipples into his mouth while he massaged my other breast in his hand. He was sucking and pulling at the bud like he couldn’t get enough. This was one of the best feelings in the world.  
While Sam was swirling and sucking at my nub, I saw Dean smiling at me looking vulnerable under his brother. I looked and even through his sweatpants I could see he was getting hard. So, I thought I would have a little bit more fun with this.  
I reached down and dragged my finger across Sam’s bulge, which earned me a moan. He then started to kiss down my stomach, stopping just above where my jeans were. He slowly started to unbutton them, then he pulled both my jeans and my panties down completely exposing me. He went to go take his pant off, but that’s where I took back control.  
“No, leave them on. I want to just feel those fingers for now. I can only imagine how good they feel curling inside me. I’m getting wet just thinking about it.”  
“No more imagining. Let me show what they can do. First I want to know what this sweet little pusy of yours tastes like. I bet it’s just as sweet as it looks.” This was a whole new side of Sam I’ve never seen before, and I was so turned on by it. The longer he talked like that the more wet I got.  
“Do whatever you want baby. I’m all yours.” That earned a glare from Dean which wasn’t quite what I was looking for, but I was going to get him to touch himself somehow.  
Sam kissed all the way down and took my clit into his mouth which earned him a moan. He started licking and sucking which sent waves of pleasure throughout my body. Then he stuck his tongue in my entrance, and let’s just say that was the best feeling in the world.  
“Oh Sam what a naughty, naughty mouth you have. That tongue is amazing, and I thought it was just good for speaking nerdy sentences.”  
“You taste so much better than you look. You taste just like honey, and man do I love honey.”  
He continued to lick and suck my sensitive spot. As he did I couldn’t help but watch Dean. He wanted to touch himself so bad, so I gave him a little nod of approval, and immediately his hand was down his pants.  
Between watching Dean touch himself, and the way Sam’s tongue moved, it almost became too much.  
“Sammy, use those fingers of yours. I want to feel them curl. I want to clench around them. Then you can lick up my juices with that dirty little tongue of yours.”  
He followed directions and immediately slipped two fingers in. He pumped them in and out curling them. I thought his tongue felt good, those long fingers were like magic. It wasn’t long before I came around them, and he licked every last bit of juice I had.  
“Man, I thought you tasted good before. That was nothing compared to what I just tasted. I didn’t think that was possible.”  
“Oh believe it.” I said getting up from the bed going over to Dean and sticking my hand down his pants to kind of help him a little.  
I pumped him slow which always got him to cum faster. But I needed him to cum even faster because my pussy wanted to feel him and I wanted to see what Sam has been hiding from me all these years.  
“Let me help you babe. I think I have just what you need.”  
I pulled his sweatpants down, and got down to where I was eye level with his cock. I licked all the way up his shaft and sucked the bead of pre-cum on his tip, then took him into my mouth. I rubbed my tongue all the way down his shaft, and sucked in, dragging my teeth all the way back up again at a very slow pace. Dean was like putty in my hands. I knew all the ways to get him to cum in 5 seconds flat. Three or four times of rubbing my tongue all the way down, then sucking and dragging my teeth back up his shaft, would be enough for him come undone for me.  
I knew every kink he had, and I would always use it against him. It wasn’t that hard to find these things out though. The first year we were together that’s pretty much all we did. I would tease him so badly while Sam was in the room and the minute Sam would leave his hands were all over me. I spent that entire year figuring out what made him tick.  
“Oh I love that pretty little mouth baby. It feels so good around my aching cock.”  
He came faster than I thought he would and man do I love the taste of his sweet seed.  
“Especially when you swallow my seed it feels so good.”  
“Enough talk more action,” I turned toward Sam now who looked all too eager to watch, “now Sam stand up.”  
He obeyed like I knew he would. Sometimes I wish Dean would listen to me as well as his brother does. I leaned up and kissed him. As we kissed I moved my hands down to unbutton his jeans. I snaked my hand down his pants and started to pump him in my hands.  
“Hmm...your hand feels so good.” He moaned into my lips.  
“Dean lay down on the bed.” I ordered disconnecting from Sam’s lips.  
I turned back to Sam and pulled his pants and boxers down revealing to me what I’ve been waiting for, for a while now. Sam’s cock looked to be a little bit longer than Dean’s, but bigger in every sense of the word.  
Dean had walked over and laid on his back while I finished undressing Sam. I walked over and got on the bed afterwards. I turned my back away from Dean and helped him align himself at my entrance. I slowly lowered myself only getting half way due to how I was positioned on the bed.  
“Come here Sam.” He walked over to where I was and I grabbed his cock and started to pump him, “you can go ahead Dean,” and he started to thrust into my core hitting just right the first try. I would squeeze down Sam’s shaft, then lightly brush up following Dean’s thrusts. It was okay for a while, but I wanted to taste Sam not just feel him. I started to lick the head of his cock swirling circles and licking up the beads of pre-cum.  
I wanted to try and see if what worked with Dean would work with Sam, so as I went down, I rubbed my tongue down his shaft, and as I went up, sucked in and dragged my teeth. That seemed to do the trick for him, but I wanted him to feel different than when I have sex with Dean, so I matched pace with Dean. It was a little harder with Sam because not all of him would fit into my mouth, so I pumped what I couldn’t put in mouth with my hands.  
“Baby you’re so tight. I didn’t think it had been that long?” Dean spoke up as he continued to thrust deeper and deeper into me.  
It wasn’t long after I put Sam into my mouth that he came. I licked every last bit of cum produced before I turned around Dean’s cock now facing the older Winchester. He stopped thrusting and let me do all the work. I was rolling my hips while he held my waist to help me a little bit. I brushed my lips against his before lightly connecting them in a passionate kiss. The whole world seemed to disappear. No matter who I let have their way with me I know that the man inside me right now is the only one for me.  
“Oh Y/N. I love what you do to me.” He moaned out, his head falling deeper into the pillows.  
I felt a twitch and then the hot seed pouring out of his cock. I continued to roll my hip against his knowing I wasn’t far behind. Sure enough a few minutes later I followed clenching around him.  
“Dean we need to do this more often. I miss doing this with you.” I said getting up off him so he could get off the bed.  
“Yeah me too. Maybe we will do it more often this year. I’m gonna go shower and wash up. Have fun with her Sammy, just not too much fun. Remember she still belongs to me.”  
“Got it.” I almost forgot Sam was in the room until Dean acknowledged him.  
Sam walked over to me cupping my face in his hands and leaning down to kiss me. At first it was soft, but it soon got rough. He turned me around and bent me over the foot of the bed.  
“Now it’s my turn to dominate you. I know you don’t want Dean to think you can be dominated, but man. The thoughts that have been running through my head. Watching you fuck my brother while that ass jiggled. It took everything I had not to stick my thick cock in your ass.” He whispered in my ear, and I could already feel myself starting to get wet.  
“I want to pound you so hard you can hardly walk. I want to feel your ass clench around me. If you miss behave though I will punish you understand?”  
I didn’t know what to say. This was a whole different Sam than what I saw 30 minutes ago. I didn’t know whether to be scared or turned on. “Understand.” I responded hoping that was what he wanted to hear. That was up until my ass started to sting.  
“Wrong.”  
“I understand sir.”  
He spread my ass cheeks and then he stuck himself inside me. It hurt at first, but then he started to thrust in and out, and it felt a little better. He started slow, but the more relaxed I felt, then the hard he would thrust.  
“Oh Y/N/N, your ass is so tight. Doesn’t Dean stretch you out?”  
“He...he hasn’t...for a while,” I moaned  
Sam continued to thrust faster and harder. I thought that he was insane trying to fit himself into my tight ass with his huge cock, but the longer he was in there the better it felt. All the pleasure built up and soon my ass was clenching around him. He continued to thrust deeper though despite how close I knew he was to the edge. Soon he was pulling out and his seed dripping into my ass.  
“Flip over.”  
I did as he told me getting a taste of my own medicine now. I pushed myself further up the bed so I wasn’t uncomfortable.  
“Spread your legs. I want to see that glorious cunt of yours.”  
Again I did as I was told and spread my legs. He started to tease me with his cock as he rubbed it over my sensitive bud. He held my hands above my head and slid into me. I wasn’t sure if I was going to be able to take him all, but he made himself fit. He thrusted in and out, faster and faster, harder and harder. He was trying to get me to moan his name. The faster he went the more pleasure shot through my body. He moved one of his hands down and started to rub circles around my bud.  
“Sam...please. That feels...s-so good.” I was gonna go over the edge again. This was even better than I imagined it to be.  
“I want you to scream my name when you cum. Loud and clear so Dean knows that it’s me having all the fun with you while he sits and waits.”  
Each sentence was punctuated with a thrust the last one hitting my g-spot. Once he found it he wanted to hit it over and over again. That sent me over the edge for the fourth time tonight.  
“Sammy, that feels so good.”  
“I know baby. I love how you feel when you clench around me. That feels good.” He was breathing heavy telling me he was getting close to his climax.  
He started to get sloppy with his thrusts and soon I felt him pull out and his seed dripped down into the valley of my ass.  
This time with Sam was really amazing. It was a fantasy that became reality, and it felt nice to be dominated by someone.  
“Thanks for including me, or well thinking about me. Sometimes I feel you forget about me when you’re with Dean.”  
“I will never forget about you. Yeah I love your brother, but you will always be my best friend.”  
He had put his pants back on and was going to walk out of my room, but before he walked out, as I was putting my clothes back on he walked over, and kissed the top of my head.  
“I’ll see you and Dean in the morning. I hope you two have an amazing anniversary.” He said smiling before walking out.  
Just as Sam walked out Dean walked in. I was still in my bra, but once he was all the way in the room he ran to me, grabbed my face, and kissed me.  
“Okay what’s up with you?”  
“Nothing. It’s just I hope he knows, and that you know, you’re still mine.”  
“Of course he knows, and obviously I know. I wouldn’t trade you for all the sex in the world trust me. When it was just the two of us I completely forgot that Sam was even in the room. I was so focused on you.”  
“Good to know. Now why don’t you go put on some nice clothes, so we can continue with tradition. You might find you have one more round in there.”  
“I always have one more round for you Dean.”  
“Great because you’re gonna need it. By the way what made you want Sam to join us?”  
“I don’t know I think The Devil Made Me Do It.”  
“I hope you know you’re not being funny.”  
“Oh I think I am though.”  
“Whatever just get ready so I can bang that pretty little ass of yours a few more times.”


End file.
